Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-01-24
2001-05-22
Morris, Patricia L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S394000, C548S302100, C548S304700
Reexamination Certificate
active
06235765
ABSTRACT:
The present invention relates to novel benzimidazole derivatives, to a process for their preparation and to their use as microbicides in crop protection and in the protection of materials.
It is already known that certain benzimidazole derivatives have fungicidal properties (cf. DE-A 4 139 950 and EP-A 0 517 476). Thus, for example 2-cyano-1-dimethylaminosulphonyl-6,6,7,7-tetrafluoro-[1,4]dioxino[2,3-f]benzimidazole and 2-cyano-6,6-difluoro-1-dimethylaminosulphonyl-[1,3]dioxolo[4,5-f]benzimidazole can be used for controlling fungi. The activity of these compounds is good, but in some cases leaves something to be desired at low application rates.
This invention, accordingly, provides novel benzimidazole derivatives of the formula
in which
X
1
, X
2
, X
3
and X
4
independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, optionally substituted cycloalkyl, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, represent
or —Z—R
5
in which
R
3
and R
4
independently of one another each represent hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted arylsulphonyl, optionally substituted arylaminocarbonyl or optionally substituted arylmethylsulphonyl or
R
3
and R
4
together with the nitrogen atom that they are attached to represent an optionally alkyl-substituted heterocyclic ring which may contain an additional oxygen atom or an aklylimino group,
Q represents a direct bond or a carbonyl group,
R
5
represents optionally substituted aryl or represents optionally substituted heterocyclyl and
Z represents a direct bond, represents CH
2
, O, S, SO, SO
2
, CO or an azo group or
represents —CO—O—, where the oxygen atom is linked to the aryl or heterocyclyl radical, or
represents —SO
2
—O—, where the sulphur atom is linked to the aryl or heterocyclyl radical, or
represents —S—CH
2
—SO
2
—, where the sulphur atom of the thio group is linked to the aryl or heterocyclyl radical, or
X
2
and X
3
together represent an optionally substituted alkylene chain having 3 or 4 members wherein one or two (non-adjacent) carbon atoms may be replaced by oxygen atoms,
R
1
represents cyano or the groupings
or
in which
R
6
represents alkyl, halogenoalkyl or optionally halogen- and/or halogenoalkyl-substituted benzyl,
R
2
represents optionally substituted heterocyclyl and
Y represents a direct bond, represents —CH
2
—, —CH
2
—CH
2
—, —CO—, —SO
2
—, —CO—O— or —SO—O— where in the case of the last two groups the carbon atom or the sulphur atom is linked to the nitrogen atom of the imidazole ring,
and acid addition salts and metal salt complexes thereof.
Furthermore, it was found that benzimidazole derivatives of the formula (I) and acid addition salts and metal salt complexes thereof are obtained when cyanobenzimidazoles of the formula
in which
X
1
, X
2
, X
3
and X
4
are each as defined above
are reacted with halides of the formula
Hal—Y—R
2
(III)
in which
R
2
and Y are each as defined above and
Hal represents chlorine or bromine,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, and the resulting benzimidazoles of the formula
in which
R
2
, Y, X
1
, X
2
, X
3
and X
4
are each as defined above
are, if appropriate, either
a) reacted with hydrogen sulphide in the presence of an acid binder and in the presence of a diluent, or
b) reacted with a sulphur compound of the formula
H—S—R
6
(IV)
in which
R
6
is as defined above
in the presence of an acid binder and in the presence of a diluent,
and an acid or a metal salt is, if appropriate, added to the resulting compounds of the formula (I).
Finally, it was found that the benzimidazole derivatives of the formula (I) and acid addition salts and metal salt complexes thereof have very good microbicidal properties and can be used in crop protection and in the protection of materials.
Surprisingly, the compounds according to the invention have better fungicidal activity than 2-cyano-1-dimethylaminosulphonyl-6,6,7,7-tetrafluoro-[1,4]dioxino-[2,3-f]benzimidazole and 2-cyano-6,6-difluoro-1-dimethylaminosulphonyl-[1,3]-dioxolo[4,5-f]benzimidazole, which are compounds of the prior art of a similar structure and of the same direction of action.
A general definition of the compounds according to the invention is given by the formula (I).
X
1
, X
2
, X
3
and X
4
independently of one another each preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkoxy having 1 to 8 carbon atoms, straight-chain or branched halogenoalkoxy having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylthio having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylthio having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylsulphinyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphinyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphonyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of halogen and alkyl having 1 to 4 carbon atoms, represent hydroxycarbonyl, alkylcarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, alkoxycarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkoxy moiety, cycloalkylcarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, cycloalkoxycarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, represent
or —Z—R
5
.
R
3
and R
4
independently of one another each preferably represent hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, aryl having 6 to 10 carbon atoms, arylcarbonyl having 6 to 10 carbon atoms in the aryl moiety, arylsulphonyl having 6 to 10 carbon atoms, arylaminocarbonyl having 6 to 10 carbon atoms in the aryl moiety or represent arylmethylsulphonyl having 6 to 10 carbon atoms in the aryl moeity, it being possible for each of the abovementioned aryl radicals to be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylsulphinyl having 1 to 4 carbon atoms, alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms.
R
3
and R
4
together with the nitrogen atom that they are attached to additionally preferably represent a heterocyclic ring having 5 or 6 ring members which is o
Assmann Lutz
Kugler Martin
Marhold Albrecht
Stenzel Klaus
Bayer Aktiengesellschaft
Morris Patricia L.
Norris & McLaughlin & Marcus
LandOfFree
Benzimidazole derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Benzimidazole derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Benzimidazole derivatives will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2536869